Switching of Aromatic Free Base Triphyrin(2.1.1) to Antiaromatic Phosphorus(V) Complexes of Triphyrin(2.1.1)

摘要

The aromatic 14 pi meso-tetraaryl triphyrin(2.1.1)s were switched to stable antiaromatic 16 pi P(V) complexes of triphyrin(2.1.1) by refluxing free base triphyrin(2.1.1)s with PCl3 in a mixture of solvents toluene/triethylamine for 4 h. The P(V) triphyrin(2.1.1)s were characterized by high-resolution mass spectrometry (HRMS) and nuclear magnetic resonance (NMR) spectroscopy and their properties were studied in detail by absorption, electrochemical, and density functional theory (DFT) studies. The studies suggested that PCl3 reduces 14 pi triphyrins to 16 pi triphyrins, which were then complexed to form stable antiaromatic P(V) complexes.